


The Hustle

by FionaFoe



Category: Supernatural
Genre: F/M, Shameless Smut, Smut, slightly kinky
Language: English
Status: In-Progress
Published: 2016-04-08
Updated: 2016-05-06
Packaged: 2018-06-01 01:38:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,951
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6495697
Author URL: https://archiveofourown.org/users/FionaFoe/pseuds/FionaFoe
Summary: <blockquote class="userstuff">
              <p>The reader spends her summer nights working in her father's roadhouse. The sexy regular, John Winchester, stays late hustling pool. What will you think of to wipe that smug look off his face?</p>
            </blockquote>





	1. Part 1

**Author's Note:**

> Written for faith-in-dean's (on tumblr) April writing challenge.  
> Prompt: "Two can play this game"
> 
> On tumblr: http://deanwinchesterswoonathon.tumblr.com/post/142309928504/the-hustle

Serving up the last of the night’s drinks at your father’s roadhouse you watched what would be the last game of pool of the night go down. You knew he would win, he always did. Every time John Winchester walked in you knew he would leave with a pile of cash he had hustled from the other patrons. It was one of those hot and sticky summer evenings, so naturally there had been a lot of ice cold beer to tap, you’d been keeping busy most of the night, walking around in your sneakers, shorts and white t-shirt serving drinks. It was just too damn hot to care about the hunters and drunks looking you over. And truth was; there was one set of eyes you didn’t mind at all.

The game went its course and by the time the sore loser stormed out John was the only one left in the joint. Even your dad had gone to bed, leaving you with the clean up. John chuckled as he leaned on the table putting his winnings away. Smug, that was what he was. 

“Win big?” You asked as you were clearing the tables.

“Yup, that will last me a week or two.” He smiled up at you, his salt and pepper beard following the movement of his lips.

There was no denying he was an attractive man. Despite his rough exterior, or maybe because of it, he oozed charm and confidence. Broad shoulders and beards were not exactly turn offs for you and neither were older men. All that summed up to that even though he was twice your age, you’d do him in a heartbeat if given the chance. But there was still the smugness, the defiant in you wanted nothing more than wipe it off his handsome face.

“Tell you what,” you took a few steps towards him, “I’ll make you a deal.”

“Oh, really now?” John smirked at you; it was almost enough to get your knees shaking.

“You play me, and if I win I get that big pile of cash.” You smiled innocently at him. You knew your way around the table really well, but he didn’t know that and that might just work to your advantage.

“And if I win?” John took a step in your direction, still relaxed and controlled.

“If you win, I’ll even out your tab.” Your words had definitely sparked his interest, and he moved over to ready the table.

\------------------------------------------------------------------------------------------------------------------------------------------------

He was good, that was for sure and you had known that from the get go. You’d just thought you were a little bit better. It looked like you might lose, but you wouldn’t give up that easy. An idea struck you; hustle him. You figured you could mess with his concentration and make him off his game. He looked away for a second and you took the opportunity to pull your t-shirt slightly further down, making sure the ladies would be good and visible when you leaned over to shoot. You walked around the table as you calculated your shot, and his line of sight. When you were sure he had the best possible view and was paying close attention to your moves, you leaned over. The puppies were good and visible and you saw John’s eyes fall to your chest. Phase one was a success; he had taken the bait. You took your shot and it was good, now it was his move. As he got in shooting position you leaned over again, resting your elbows on the table, boobs squished between your arms. John stood up straight, pool cue in hand. 

“What are you playing at, girl?” He raised his eyebrows, looking you straight in the eye.

“I’m sure I have no idea what you’re taking about.” You fluttered your lashes and stood up. Innocent was the way to go.

“Two can play this game…” His low voice rumbled in his chest. 

He started walking around the table towards you. Slow, determined steps. The bar lay quiet around you, only the creaking of his boots to be heard. His eyes were locked with yours; you had to fight your instincts to not back away. If you were being honest with yourself he was an intimidating man. The broad shoulders, brown eyes hinting at impure thoughts, the salt and pepper beard and how he oozed absolute control. Fuck. All the nerves in your body were on high alert, you were sure you could feel every atom in the air around you brush your skin. Chills ran thorough you as the distance between you shrank. Fuck, how could you feel this way? John hadn’t even touched you yet! You might as well throw your hands up in surrender. Whatever game there was to play with him… he’d surely win.

“What’s wrong sweetheart?” John stopped and tilted his head, still a few feet away from you, “you look a bit out of it…”

“No offence…” You managed to find a few whispered words deep in your belly, “but you’re kind of intimidating…”

“Now, I won’t bite…” He offered you half a smile, “unless you want me to of course. We’re not gonna do anything you don’t want to do. I’m not gonna hurt you sweetheart.”

“Okay…” You managed, feeling a bit more confident.

“So what do you want?” He asked, still standing in the same spot, “Do you want me to come over there?” He nodded in your direction.

“Yes, I do.” Your voice was a little shaky and you felt your face flush. In that moment you wanted nothing more than for him to make his way over to you. Well, maybe a few more things if you were being honest…

He continued walking over to you, keeping his slow pace. Anticipation built in the pit of your belly and finally he was there. Standing in front of you in dark jeans and a white t-shirt, showing off his toned body. He was so close you could smell him; the musk, a hint of gun oil and whiskey. The want was building in you, fast. You were done for. No going back.

“So, I’m here,” He said, you were sure you could feel the bass of his voice hit your very bones, “what more do you want? Do you want to shoot some more pool?” He nodded to the pool cue he was still holding.

“No, I want you to kiss me.” You didn’t want to wait anymore, you just needed his skin to touch yours, you needed for him to put an end to the anticipation before you combusted from lust and want.

“Well that I can do, Y/N.” His voice was still so damn controlled as he put his pool cue on the table next to you.

When he finally reached out for you and made contact with your skin it felt electric. He let his calloused hands travel up your arms, leaving a trail of goose bumps, before he took hold of your shoulders. He pulled you in and his lips met yours, instantly you melted into a needy, lusty kiss. You could taste the Johnny Walker off his perfect tongue, you felt the rough hair of his beard against your soft face. You let your arms reach under his to caress his muscular back and let your body press up against him. Never braking from the kiss John placed his hands on your hips and hoisted you up on the pool table. Sitting there you felt his hands reach around and onto your butt. A needy moan escaped your lips and he broke from the kiss.

“So now you got the kiss you wanted,” his brown eyes smiled devilishly at you, “how about I get something I want?”

“Anything,” your need colored your words, “anything you want John…”

That seemed to be all he needed to hear. He tore off your t-shirt and you raised your arms in compliance. He took a moment as he looked at you, releasing a low groan he cocked his head. You reached back to unclasp your bra, but before you had the time he stopped you.

“I’ll do it,” his eyes had gone dark with desire, “I’m in control here…” One-handed he opened your bra and let the ladies free, “damn…” he muttered as he reached out to touch, pinching a nipple, letting out a moan from you. 

He proceeded to kiss his way from your neck, traveling across your chest to your belly, he stopped as he reached your shorts. You lifted your body off the table with your arms to let him peel them off your body along with your panties. Sitting on the pool table naked you kicked off your shoes and socks, and there you were naked on the pool table as John Winchester admired your form. Soon enough he kneeled down. He placed his rough hands on your thighs and spread them, leaning in you felt his breath on your sex and you closed your eyes waiting for him. His tongue instantly found your clit. He circled it lightly to begin with, nice slow strokes. A moan escaped your lips and he took it as a sign to quicken his pace, his skilled tongue bringing you towards ecstasy. Sucking your clit lightly, he slid his index finger into your dripping pussy. You nearly screamed at the added pleasure as he found your g-spot and started brushing it as he thrust his finger in and out of you. As a second finger entered you, you felt it build and release was close.

“John,” you panted, “I’m gonna cum…”

“Go ahead girl, you’re allowed…” His words caused new vibrations on your sex and you came, hard and loud.

You still hadn’t returned to earth when he pushed you down on the pool table. You made your way all the way up and made sure the balls were out of the way. Undressing in a hurry he then followed you up on the table and made you taste yourself on his fingers, than his mouth. Kneeling next to your head he offered you his cock and you were happy to have it. It was big and hard, gorgeous really. A drop of precum had made its way to the surface, looking too delicious to pass up. It might have been the biggest cock you’d seen, you thought as you greedily licked your way from the base to the head. You struggled to breathe as he gave it a few thrusts and pulled it out. He then lowered himself on top of you and slowly entered you, guiding his cock with his hand. You gasped for air as he filled you up and started moving. His dick going deeper than anyone had ever been. You started ruffling his hair, but before long he grabbed your wrists with one of his hands and held them over your head. 

“I’m in control… Didn’t I just tell you?” He was so stern and calm it made chills run down your spine. 

His other arm reached for your right leg and placed it on his shoulder. One thrust and it hit your g-spot. Hard! You scream out and he picked up the pace, hitting your g-spot over and over. He bit at your neck, his beard brushing your collarbone, sending chills through your body. He drove you to the edge in fewer minutes than anyone ever had. As he drove you over the edge you screamed out his name, not caring if you woke the entire town.

“Did I tell you to cum?” he asked as you came down from your high. “You’re gonna pay for that.” 

John flipped you over. As you lay on your stomach he slapped your ass hard. First one cheek, then the other. He proceeded to thrust into you with force. The surprise made you scream out in pleasure. “Now next time you cum when I tell you…”

“Yes, John,” You moaned, “I’ll be good!”

You felt him lift you up on all fours. His thrusting increased and you knew you’d cum before long. With your moans increasing he slapped your ass.

“John… I’ll cum soon… Can I?” You managed to mutter.

“Hold on sweetheart…” He said through gritted teeth. You could hear in his voice he was getting ready to cum, “go ahead baby.” 

That was really all you needed to hear and you came hard. Your walls contracting sent John over the edge and he shot into you, filling you with his cum.

Lying on the pool table next to each other you tried getting back to earth. John was the first to get up. You watched him dress from the pool table, pulling on his t-shirt and jeans, stepping into his boots. He threw his worn leather jacket over his shoulder.

“Next time I’m in town… I’m fucking you again.” He chuckled at you.

“Whatever you want John. Come by any time…” You replied, winking over at the older man. 

When he was gone you remembered the bet and his tab, but fair was fair, whatever game you had been playing he had surely won.


	2. Part two

**Summary for the Chapter:**

> The reader goes about her daily life at the roadhouse, bored out of her mind, waiting for John to return.

Lately it felt like your life was on hold. Summer had turned to fall, and you were standing still. Stuck in a roadhouse in the middle of nowhere, dreaming of escape. You wanted out, didn’t want your life to be what it most likely would; you taking over the roadhouse when your dad got too old, maybe getting married to a boy from town, living and dying by the tap. You craved excitement and adventure, the closest you’d gotten was your one night escapade with John Winchester, but he hadn’t been back. You’d worked hard on pushing the man out of your mind, but it had proven a hard task even as the days turned into weeks and months. A glance over at the pool table had you vividly remembering your failed attempt at hustling him, and the antics that followed. 

“Hey!” Your dad pulled you out of your train of thought, blushing you met his eyes, “Lots of people are waiting to get served, honey. Get moving, please.”

You collected yourself and started taking orders: beer, Jim, Johnny, Jack and the odd order for vodka. It was a moderately busy night, even though it was only Thursday. Hunters drank every night of the week. No wonder you thought, with all the shit they’d been through. You found yourself wondering what it was like. You figured there would be a rush of adrenaline after killing a vamp and saving the victim, now there was an adventure! 

The night lagged on and people came and went, your eyes covertly sliding over to the door every time it opened. Would tonight be the night? You had just about given up all hope as your wristwatch’s short arm hit ten pm, but then it happened. The door creaked open, and you glanced over, your eyes meeting a broad and familiar silhouette. He smiled coyly at you as he made his way over to the bar, and you could swear your heart skipped a beat, suddenly you were overcome with nerves. You had hoped and waited, longed even, for him to walk in and when it finally happened you found yourself knocked off your feet by shyness! You turned to a hunter ordering a beer, your hands slightly shaking as you grabbed a glass and handled the tap. You handed it over to her and looked for another order to fill. Of course she was the only one asking for your attention, everyone else having drinks in hand.

“Double Johnny, sweetheart…” John smiled at you, his hazel eyes narrowing mischievously, hinting at how well he really knew you.

“Red, black or blue?” You croaked and John hummed in amusement. Fuck your nerves.

“Black,” His husky voice making the hairs on your arms stand up, “you should know that’s my usual by now, girl.”

You swallowed hard and tried to collect yourself as you turned around, standing on tiptoes reaching for the bottle. You poured his double and managed a smile at him, and he met it, his smile as gorgeous as him. Son of a bitch, you had it bad. All you wanted was for him to pick you up and carry you out the door, and fuck you on the hood of his truck.

“So, how’s it been hanging around here? Any of these old bastards been giving you a hard time the past few months?” He smiled at you, knowingly.

“It’s been fine,” you answered matter-of-factly, “a bit boring maybe.”

“Better boring than dangerous, though.” He smiled at you.

“I guess…” You answered.

You were ready to ask if he was okay, trying to get a real conversation going, when you were dragged away by another order. And then another. They kept coming and the minutes lagged on, thirsty bastards all finishing up at the same time it seemed. When you were ready to pick the convo back up again, you saw he’d walked over to shoot some pool, much to your disappointment. He walked around the table, getting ready to break. He leaned over and you felt your heartbeat pick up as you realized the table he was playing at was the very one he’d fucked you senseless on months ago. You bit your lip as he looked up meeting your eyes, devilish grin hitting his beautiful mouth. Your want was making itself evident between your legs. He was magnetic, pulling you towards him and you had to try your hardest not to stride over there, demanding him to fuck you.

You stormed off to the bathroom, needing a cold splash of water to the face and a reality check. You were at work in your dad’s roadhouse, goddamit! This was no time to loose it over John freaking Winchester! You walked back out, making your way over to the bar from across the room when you saw him walking towards you, you slowed down as he got close. You could smell him, the leather and whiskey, some gun oil. So damned sexy.

“Make an excuse, meet me outside in the parking lot.” He whispered in your ear, stopping you dead in your tracks. He, on the other hand, quickly made his way past you walking out the door.

You looked around to see if praying eyes had caught on to the quick words he had spoken to you. It seemed safe, no one were paying you much attention. You continued walking over to the bar, up to your dad who was in a deep conversation with an old friend.

“I’m gonna take out the trash.” You stated and he nodded at you before excusing himself from the conversation to tend the bar. 

Trash bags in hand you made your way out the door. You dumped them in the dumpster before looking around, trying to locate John. He was standing no more than ten feet away from you, leaning on his truck, his arms crossed across his firm chest. Slowly you walked over to him, letting your eyes travel his frame, broad and toned. When there was only a few feet separating you, he stood up and let his hands dig into his pockets.

“So…” you started, not sure what you were gonna say yet, “I excused myself, what do you want?” Your heart raced, daring to hope you were right about his wishes.

“I think you know what I want, girl.” He smirked at you, “I think I already told what was gonna happen if I walked into your bar again…” He said, nodding towards the door, making you swallow hard.

“I remember…” You replied, you voice thick with lust, “bit crowded at the moment though.”

“Funny girl,” he chuckled, “why don’t you come for a drive?”

“He’ll wonder where I am.” You answered, cursing yourself for still working for your father.

“You’ll think of something to tell him, you’re a smart girl.” He said matter-of-factly and opened the door on the driver’s side. 

John didn’t wait for you to respond. He merely got in the truck and started the engine. You only gave yourself a second to think it over before hurrying over to the passenger side, getting in his car. John Winchester was like a drug, clouding your judgment. Fuck it. You were a grown woman and in charge of your own damned life.

John drove through the darkness, the highway almost abandoned. Your eyes were glued to his handsome profile, cradled by the moonlight.

“So tell me, Winchester, where are we going?” You asked, and he met your eyes for a second, before looking back at the road.

“Well, that depends…” He smiled, “Gonna take us a few minutes to get to my motel. You down with that, sweetheart?”

“I’m so down with that…” You answered, your voice breathy.

He pulled up at his motel and led the way to his room. It was like a million other motel rooms you’d seen on family road trips, boring and worn, but it didn’t matter. You weren’t there to enjoy the surroundings; you were there for him. The moment he closed the door his lips were on yours, devoured by lust you melted into him. Your arms wrapped around each other you backed up towards the foot of the bed. You laid down, never breaking form the kiss, John’s body on your smaller frame, his weight on you. It felt amazing, you had dreamt of this since he’d walked out that night. The smell and feel of him had you exhilarated, desperate for his rough hands to graze your skin again.

“God, I’ve been longing for you for a month, baby.” He groaned, breaking from the kiss.

“Me too John…” You looked up at him, where he hovered slightly above you, “I’ve been going crazy waiting for you to walk through the door.”

“Why the hell did I wait so long?” He stood up, “Why don’t you show me what I’ve been missing out on, princess.”

You sat up on the bed, John standing in front of you. You were careful to keep eye contact as you unbuttoned your cardigan and pulled it off, next you took hold of the hem of your t-shirt, slowly pulling it up, exposing you bra. You saw John’s lower lip disappear into his mouth as you pulled it over your head. 

“Fuck, girl…” He groaned, letting his hand rub his length through his jeans. 

Next you kicked off your shoes and socks, before unbuttoning your jeans and unzipping them. Slowly, you scooted you of them and smiled innocently at him.

“Now, am I allowed to unclasp my own bra this time?” You teased.

“You’re allowed,” he chuckled, “such a good girl for asking…”

You continued to strip, unclasping your bra letting your breasts bounce free, you saw his hand tighten around the magnificent cock you knew those jeans were keeping captive. It was time for your finale. You let your fingers hook into your panties, sliding them slowly down as you sat. Completely naked you smiled brightly at him as you saw the effect your bare body had on him.

“So fucking sexy.” He said, his husky voice making your heart race.

He proceeded to get to work on his own clothes, a lot faster than you had with yours. His shirt falling to the floor in mere seconds, revealing his toned chest, sprinkled with salt and pepper hair. You resisted the need to reach out and touch, thinking there’d be time for that in a minute. Next he dropped his jeans, kicking his boots and socks off in the process.

“Why don’t you unwrap this, sweetheart?” He said, motioning to his crotch, “You’ve earned it.”

You nodded at him and hurried down on your knees, hooking your fingers into the waistband of his boxers, slowly pulling them down. His member sprung free and it was like being reunited with an old friend, the urge to give it a warm welcome causing you to kiss it instantly. A soft kiss on the head later, you let your tongue slide from the base of the shaft up his length, feeling the velvety skin with your tongue. Reaching the tip you lowered your moth on it, taking the whole impressive length in your mouth, feeling it against your throat. Sucking gently you moved up and down and soon a big hand found the back of your head, gripping your hair, urging you to speed up. Violently sucking him off, you felt the salty taste of his precum on your tongue and knew he’d make you stop soon, and he did, pulling your head off him and helping you up.

“Good girl…” He hummed and kissed you softly, “Now lie down on your back.”

You did as he ordered, and soon you were on your back as the bed creaked at the added weight of John Winchester climbing up after you, positioning himself between your thighs. You spread wider for him, and soon he had dived in, his tongue finding your clit, lapping at it hungrily. You moaned out his name as he used two fingers to tease at you entrance. 

“Want me to use those fingers to find that sweet spot, princess.” He said, the proximity of his lips and deep, resonating voice to your sex making you practically vibrate.

“Yes, please John!” You nearly scream from want.

He wasn’t hard to beg and soon he slipped them into your wet pussy. A few thrusts in and out and he hooked them slightly, finding your g-spot as promised. He pushed in and out of you, accelerating his speed, fast fingers hitting your sweet spot relentlessly.

“John… Can I come please?” You pleaded, your voice throaty and thick.

“Do it, sweetheart, show me how I make you feel.” He went back to work on your clit instantly, all while fucking you with his fingers.

You felt it build fast, knowing he wanted to see you come only made the pleasure more intense. You panted and fisted the sheets in your hands, before it rolled over you in waves, your body squirming unintentionally and you screamed out his name.

As you came back down to earth John crawled up your body, and positioned himself between your legs. Soon he guided his cock towards you entrance and you felt it graze your slick hole. His breath heavy he eased into you, making you gasp in response at the full feeling. He moved slowly at first letting your walls adjust to his size, your slick coating his cock, making it easier to move. He bit down on your neck and you moaned at him. He started moving faster and you cocked your head back at the pleasure, panting hard. He continued his biting at your skin, moving his mouth south, finding your breast. John pulled one perky nipple between his teeth and your breath hitched. You pushed against him, meeting his thrusts, his crashing into you brushing against your g-spot. You knew your next climax was close.

“John, I’m so close…” You panted at him through gritted teeth, afraid the coil would snap before he’d given permission.

“Oh, really?” He teased and slammed harder into you, you started seeing stars, desperate for release.

“Yes!” You screamed at him.

“So desperate,” he groaned at you, “count to ten for me, and I’ll let you come.”

“One, two,” you started, “three, four, five,” you concentrated hard, “six, seven,” you felt the room spin, “eight, nine,” you’d soon have your release, “ten!” 

You screamed out and felt your walls clench around John’s impressive girth. He was right behind you and you felt him twitch inside you, before filling you up.

For a little while you just lay together, coming down off your high. Breathing deep together, you closed your eyes wanting nothing more than fall asleep on his chest, breathing him in. But alas, reality dawned on you. You had to get back to the roadhouse. Fast. You leaped up, frantically digging your clothes up from the pile on the floor.

“What’s the rush, princess?” John asked lazily.

“I’ve got to get back. I was taking out the trash remember?” You answered checking your watch, “And that was over an hour ago!”

“Okay, calm down.” He got up from the bed, “I’ll drive you back right away.”

“Where the hell have you been?” Your dad’s voice shot out at you as you walked in through the back door, slipping a note with John’s number into your pocket, “I thought you were just taking out the trash!”

“I needed some air, so I took a walk…” You avoided his eyes, afraid he’d spot your lie.

“Bullshit... Since when do you just leave the bar at its busiest to take a fucking two hour long walk?” He scowled at you.

“Since mind your own business! Besides, it’s only been an hour and a half!” You spat back at him.

“Don’t you take that tone with me, young lady! You’re the one sneaking off, if one of these guys even laid a hand on you-”

“Oh my God, stop treating me like a fucking child!” You interrupted him, you did not need to hear the end of that sentence. You knew full well that if he found out you’d hooked up with a regular, not to mention one twice your age, there would be hell to pay. “Now are you gonna get out my way and let me do my job?” You asked and pushed your way past him, knowing full well he’d start keeping a closer eye on you from now on.


End file.
